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2,4-dibromophenol + bromide + H2O2
2,4,6-tribromophenol + 2 H2O
-
-
-
?
2-chloro-5,5-dimethyl-1,3-cyclohexane-dione HBr + H2O2
? + 2 H2O
2-chloro-5,5-dimethyl-1,3-cyclohexane-dione (mcd) is the standard substrate for the determination of haloperoxidase activity using H2O2 as the oxidant
-
-
?
2-chlorodimedone + chloride + H2O2
1,1-dimethyl-4,4-dichloro-3,5-cyclohexanedione + 2 H2O
model substrate monochlorodimedone, activity of EC 1.11.1.10
-
-
?
4-bromophenol + bromide + H2O2
2,4-dibromophenol + 2 H2O
-
-
-
?
beta-estradiol + bromide + H2O2
? + 2 H2O
-
-
-
?
beta-estradiol + chloride + H2O2
? + 2 H2O
-
-
-
?
Br- + H2O2 + (3E,6R,7R)-laurediol
deacetyllaurencin + H2O
-
-
-
-
?
Br- + H2O2 + (3R)-3-bromo-2,6-dimethylhept-5-en-2-ol
3,5-dibromo-2,6-dimethylheptane-2,6-diol + H2O
-
-
70% yield, at pH 6.0
-
?
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
?
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
bromochlorodimedone + ?
-
i.e. monochlorodimedone
-
-
?
Br- + H2O2 + 1-methoxynaphthalene
1-methoxy-4-bromonaphthalene + H2O
-
-
-
-
?
Br- + H2O2 + 1-phenylpent-4-en-1-ol
4-bromo-1-phenylpentane-1,5-diol + 5-bromo-1-phenylpentane-1,4-diol + 2-(bromomethyl)-5-phenyltetrahydrofuran + H2O
-
-
30% yield of 4-bromo-1-phenylpentane-1,5-diol, 28% yield of 5-bromo-1-phenylpentane-1,4-diol, and 25% yield of 2-(bromomethyl)-5-phenyltetrahydrofuran, at pH 6.0
-
?
Br- + H2O2 + 2,4,6-tribromophenol
1,3,6,8-tetrabromodibenzo-p-dioxin
-
formation of ppb-level yields of 1,3,6,8-tetrabromodibenzo-p-dioxin through direct condensation. Additionally, 1,3,7,9-tetrabromodibenzo-p-dioxin, 1,2,4,7-tetrabromodibenzo-p-dioxin, and/or 1,2,4,8-tetrabromodibenzo-p-dioxin and 1,3,7-tribromodibenzo-p-dioxin and 1,3,8-tribromodibenzo-p-dioxin are frequently formed but at lower yields. Reaction probably proceeds via bromine shifts or Smiles rearrangements, whereas the tribromodibenzo-p-dioxins may result from subsequent debromination processes
-
?
Br- + H2O2 + 2-hydroxybenzyl alcohol
2,4,6-tribromobenzyl alcohol + H2O
-
-
-
-
?
Br- + H2O2 + 2-methoxyphenol
2-bromo-6-methoxyphenol + 4-bromo-6-methoxyphenol + H2O
-
56% of product, in a 21/79 mixture of o-/p-regioisomers, plus 10% 2,4-dibromo-6-methoxyphenol
-
?
Br- + H2O2 + 2-methylphenol
2-bromo-6-methylphenol + 4-bromo-6-methylphenol + H2O
-
68% of product, in a 16/84 mixture of o-/p-regioisomers, plus 4% 2,4-dibromophenol
-
?
Br- + H2O2 + 2-t-butylphenol
2-bromo-6-t-butylphenol + 4-bromo-6-t-butylphenol + H2O
-
42% of product, in a 36/64 mixture of o-/p-regioisomers, plus 2% 2,4-dibromo-6-t-butylphenol
-
?
Br- + H2O2 + 4-pentynoic acid
(5E)-bromomethylidenetetrahydro-2-furanone
-
catalyzes the bromolactonization of 4-pentynoic acid forming (5E)-bromomethylidenetetrahydro-2-furanone. Formation of the bromofuranone likely results from an initial bromination reaction at the terminal alkyne, followed by cyclization from intermolecular nucleophilic attack by the terminal hydroxyl group
-
-
?
Br- + H2O2 + 5-methyl-1-phenylhex-4-en-1-ol
4-bromo-5-methyl-1-phenylhexane-1,5-diol + 2-(1-bromo-1-methylethyl)-5-phenyltetrahydrofuran + 3-bromo-2,2-dimethyl-6-phenyltetrahydro-2H-pyran + H2O
-
-
69% yield of 4-bromo-5-methyl-1-phenylhexane-1,5-diol, 6% yield of 2-(1-bromo-1-methylethyl)-5-phenyltetrahydrofuran, and 9% yield of 3-bromo-2,2-dimethyl-6-phenyltetrahydro-2H-pyran, at pH 6.0
-
?
Br- + H2O2 + aniline
o-bromoaniline + p-bromoaniline + ?
Br- + H2O2 + anisole
p-bromoanisole + o-bromoanisole + H2O
-
-
-
-
?
Br- + H2O2 + cyclohexene
trans-1-hydroxy-2-bromocyclohexane
-
-
-
-
?
Br- + H2O2 + cytidine
5-bromocytidine + H2O
-
-
-
-
?
Br- + H2O2 + cytosine
5-bromocytosine + H2O
-
-
-
-
?
Br- + H2O2 + methyl pyrrole-2-carboxylate
methyl 4-bromo-1H-pyrrole-2-carboxylate + methyl 5-bromo-1H-pyrrole-2-carboxylate + H2O
-
quantitative conversion within 24 h, 94% of product in 93/7 ratio of 4-/5-substituted regioisomers
-
?
Br- + H2O2 + methyl pyrrole-2-carboxylate
methyl 5-amino-4-bromocyclopenta-1,3-diene-1-carboxylate + methyl 5-amino-3-bromocyclopenta-1,3-diene-1-carboxylate + methyl 5-amino-3,4-dibromocyclopenta-1,3-diene-1-carboxylate + H2O
-
-
5% yield of methyl 5-amino-4-bromocyclopenta-1,3-diene-1-carboxylate, 59% yield of methyl 5-amino-3-bromocyclopenta-1,3-diene-1-carboxylate, and 5% yield of methyl 5-amino-3,4-dibromocyclopenta-1,3-diene-1-carboxylate, at pH 6.3 and 25°C
-
?
Br- + H2O2 + monochlorodimedon
?
-
-
-
?
Br- + H2O2 + monochlorodimedone
?
-
-
-
-
?
Br- + H2O2 + monochlorodimedone
? + H2O
Br- + H2O2 + monochlorodimedone
H2O + ?
-
-
-
-
?
Br- + H2O2 + monochlorodimedone
monobromo-monochlorodimedone + H2O
-
-
-
-
?
Br- + H2O2 + o-dianisidine
?
Br- + H2O2 + phenol
2,4,6-tribromophenol + H2O
-
-
-
-
?
Br- + H2O2 + phenol
2-bromophenol + 4-bromophenol + H2O
-
69% of product, in a 91/9 mixture of o-/p-regioisomers, plus 3% 2,4-dibromo-6-methylphenol and some 2,4,6-tribromophenol
-
?
Br- + H2O2 + phenol red
phenol blue + ?
-
-
-
-
?
Br- + H2O2 + pyrazole
4-bromopyrazole + H2O
-
-
-
-
?
Br- + H2O2 + styrene
DL-1 -bromo-2-hydroxy-2-phenylethane + H2O
-
-
-
-
?
Br- + H2O2 + thiophene
2-bromothiophene + H2O
-
-
-
-
?
Br- + H2O2 + trans-cinnamic acid
(+/-)-erythro-2-bromo-3-hydroxy-3-phenylpropionic acid + H2O
-
-
-
-
?
Br- + H2O2 + trans-cinnamyl alcohol
(+/-)-1,3-dihydroxy-2-bromo-3-phenylpropane + H2O
-
-
-
-
?
Br- + H2O2 + uracil
5-bromouracil + H2O
-
-
-
-
?
Capso + Br- + peracetic acid
?
carvacrol + chloride + H2O2
? + 2 H2O
-
-
-
?
cyclohexene + HBr + H2O2
? + 2 H2O
cytosine + Br- + peracetic acid
5-bromocytosine + ?
equiline + bromide + H2O2
? + 2 H2O
-
-
-
?
equiline + chloride + H2O2
? + 2 H2O
-
-
-
?
estradiol + 2 bromide + 2 H2O2
2,4-dibromo beta-estradiol + 4 H2O
-
-
-
?
estradiol + 2 chloride + 2 H2O2
2,4-dichloro beta-estradiol + 4 H2O
-
-
-
?
estradiol + bromide + H2O2
2-bromo beta-estradiol + 2 H2O
-
-
-
?
estradiol + bromide + H2O2
4-bromo beta-estradiol + 2 H2O
-
-
-
?
estradiol + chloride + H2O2
2-chloro beta-estradiol + 2 H2O
-
-
-
?
estradiol + chloride + H2O2
4-chloro beta-estradiol + 2 H2O
-
-
-
?
estrone + bromide + H2O2
? + 2 H2O
-
-
-
?
estrone + chloride + H2O2
? + 2 H2O
-
-
-
?
Hepes + Br- + peracetic acid
?
hesperetin + chloride + H2O2
? + 2 H2O
-
-
-
?
I- + H2O2 + monochlorodimedone
? + H2O
-
-
-
?
I- + H2O2 + o-dianisidine
?
I- + H2O2 + pyrazole
4-iodopyrazole + H2O
-
-
-
-
?
I- + H2O2 + uracil
5-iodouracil + H2O
-
-
-
-
?
indene + HBr + H2O2
? + 2 H2O
KBr + 2 H2O
KH + HBr + H2O2
-
-
-
?
monochlorodimedone + Br- + H2O2
?
monochlorodimedone + HBr + H2O2
monobromomonochlorodimenone + 2 H2O
Mops + Br- + peracetic acid
5-bromocytosine + ?
naringenin + chloride + H2O2
? + 2 H2O
-
-
-
?
nerol + HBr + H2O2
? + 2 H2O
-
-
-
?
phenol + bromide + H2O2
4-bromophenol + 2 H2O
-
-
-
?
phenol + H2O2 + Br-
4-bromophenol + 2-bromophenol + H2O
-
-
4-bromophenol + 2-bromophenol at the ratio of 4:1
-
?
pyrene + chloride + H2O2
? + 2 H2O
-
-
-
?
RH + Br- + H2O2 + H+
RBr + 2 H2O
RH + bromide + H2O2
RBr + 2 H2O
-
-
-
?
RH + HBr + H2O2
RBr + 2 H2O
RH + I- + H2O2 + H+
RI + 2 H2O
-
-
-
?
taurine + Br- + peracetic acid
bromotaurine + ?
Tes + Br- + peracetic acid
?
thymol + chloride + H2O2
? + 2 H2O
-
-
-
?
thymolsulfonphthalein + HBr + H2O2
? + 2 H2O
-
-
-
?
Tris + Br- + peracetic acid
?
[6-(4'-amino)phenoxy-3H-xanthen-3-on-9-yl]benzoic acid + Br- + H2O2 + H+
? + 2 H2O
additional information
?
-
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
?
-
i.e. monochlorodimedone
-
-
?
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
?
i.e. monochlorodimedone
-
-
?
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
?
-
i.e. monochlorodimedone
-
-
?
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
?
-
i.e. monochlorodimedone
-
-
?
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
?
-
i.e. monochlorodimedone
-
-
?
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
?
-
i.e. monochlorodimedone
-
-
?
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
?
i.e. monochlorodimedone
-
-
?
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
?
-
i.e. monochlorodimedone
-
-
?
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
?
-
i.e. monochlorodimedone
-
-
?
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
?
-
i.e. monochlorodimedone. Requirement of a catalytic triad in the halogenation mechanism
-
-
?
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
?
-
i.e. monochlorodimedone
-
-
?
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
?
-
i.e. monochlorodimedone
-
-
?
Br- + H2O2 + 1,1-dimethyl-4-chloro-3,5-cyclohexanedione
?
-
i.e. monochlorodimedone
-
-
?
Br- + H2O2 + aniline
o-bromoaniline + p-bromoaniline + ?
-
no activity in absence of Br-
-
-
?
Br- + H2O2 + aniline
o-bromoaniline + p-bromoaniline + ?
-
in absence of Br- the enzyme oxidizes aniline via azobenzene and azoxybenzene finally into nitrobenzene
-
-
?
Br- + H2O2 + monochlorodimedone
? + H2O
-
-
-
?
Br- + H2O2 + monochlorodimedone
? + H2O
-
-
-
?
Br- + H2O2 + monochlorodimedone
? + H2O
-
-
-
?
Br- + H2O2 + monochlorodimedone
? + H2O
-
-
-
-
?
Br- + H2O2 + o-dianisidine
?
-
-
-
?
Br- + H2O2 + o-dianisidine
?
-
-
-
?
Capso + Br- + peracetic acid
?
-
-
-
-
?
Capso + Br- + peracetic acid
?
-
-
-
-
?
cyclohexene + HBr + H2O2
? + 2 H2O
-
-
-
?
cyclohexene + HBr + H2O2
? + 2 H2O
-
-
-
?
cytosine + Br- + peracetic acid
5-bromocytosine + ?
-
-
-
-
?
cytosine + Br- + peracetic acid
5-bromocytosine + ?
-
-
-
-
?
Hepes + Br- + peracetic acid
?
-
-
-
-
?
Hepes + Br- + peracetic acid
?
-
-
-
-
?
I- + H2O2
triiodide + ?
-
-
-
-
?
I- + H2O2
triiodide + ?
-
-
-
?
I- + H2O2 + o-dianisidine
?
-
-
-
?
I- + H2O2 + o-dianisidine
?
-
-
-
?
indene + HBr + H2O2
? + 2 H2O
-
-
-
?
indene + HBr + H2O2
? + 2 H2O
-
-
-
?
monochlorodimedone + Br- + H2O2
?
-
-
-
-
?
monochlorodimedone + Br- + H2O2
?
-
-
-
-
?
monochlorodimedone + HBr + H2O2
monobromomonochlorodimenone + 2 H2O
-
-
-
?
monochlorodimedone + HBr + H2O2
monobromomonochlorodimenone + 2 H2O
the monochlorodimedone stable enol form exists as an enolic anion without the ketoic isomer at reaction pH 5.0
-
-
?
monochlorodimedone + HBr + H2O2
monobromomonochlorodimenone + 2 H2O
the monochlorodimedone stable enol form exists as an enolic anion without the ketoic isomer at reaction pH 5.0
-
-
?
Mops + Br- + peracetic acid
5-bromocytosine + ?
-
-
-
-
?
Mops + Br- + peracetic acid
5-bromocytosine + ?
-
-
-
-
?
RH + Br- + H2O2 + H+
RBr + 2 H2O
-
-
-
?
RH + Br- + H2O2 + H+
RBr + 2 H2O
-
-
-
?
RH + Br- + H2O2 + H+
RBr + 2 H2O
-
-
-
?
RH + Br- + H2O2 + H+
RBr + 2 H2O
-
-
-
-
?
RH + Br- + H2O2 + H+
RBr + 2 H2O
-
-
-
-
?
RH + Br- + H2O2 + H+
RBr + 2 H2O
-
-
-
-
?
RH + Br- + H2O2 + H+
RBr + 2 H2O
-
-
-
-
?
RH + HBr + H2O2
RBr + 2 H2O
-
-
-
?
RH + HBr + H2O2
RBr + 2 H2O
-
-
-
?
RH + HBr + H2O2
RBr + 2 H2O
-
-
-
?
taurine + Br- + peracetic acid
bromotaurine + ?
-
-
-
-
?
taurine + Br- + peracetic acid
bromotaurine + ?
-
-
-
-
?
Tes + Br- + peracetic acid
?
-
-
-
-
?
Tes + Br- + peracetic acid
?
-
-
-
-
?
Tris + Br- + peracetic acid
?
-
-
-
-
?
Tris + Br- + peracetic acid
?
-
-
-
-
?
[6-(4'-amino)phenoxy-3H-xanthen-3-on-9-yl]benzoic acid + Br- + H2O2 + H+
? + 2 H2O
the conversion of non-fluorescent APF to fluorescein through the production of HOBr by V-BrPO of is shown by increases in fluorescence following the addition of H2O2 to the enzyme assay mixture at approximately 50 s after initiation of data collection
-
-
?
[6-(4'-amino)phenoxy-3H-xanthen-3-on-9-yl]benzoic acid + Br- + H2O2 + H+
? + 2 H2O
-
-
-
-
?
[6-(4'-amino)phenoxy-3H-xanthen-3-on-9-yl]benzoic acid + Br- + H2O2 + H+
? + 2 H2O
-
-
-
-
?
[6-(4'-amino)phenoxy-3H-xanthen-3-on-9-yl]benzoic acid + Br- + H2O2 + H+
? + 2 H2O
-
-
-
-
?
[6-(4'-amino)phenoxy-3H-xanthen-3-on-9-yl]benzoic acid + Br- + H2O2 + H+
? + 2 H2O
-
-
-
-
?
additional information
?
-
enzyme uses hydrogen peroxide and bromide yielding molecular bromine as reagent for electrophilic hydrocarbon bromination
-
-
?
additional information
?
-
protein binding through the enzyme occurs primarily through hydrogen bridges and superimposed by Coulomb attraction according to thermochemical model on density functional level of theory. The strongest attractor is the arginine side chain mimic N-methylguanidinium, enhancing in positive cooperative manner hydrogen bridges toward weaker acceptors, such as residues from lysine and serine. Hydrogen peroxide activation occurs in the thermochemical model by side-on binding in orthovanadium peroxoic acid, oxidizing bromide with virtually no activation energy to hydrogen bonded hypobromous acid
-
-
-
additional information
?
-
-
protein binding through the enzyme occurs primarily through hydrogen bridges and superimposed by Coulomb attraction according to thermochemical model on density functional level of theory. The strongest attractor is the arginine side chain mimic N-methylguanidinium, enhancing in positive cooperative manner hydrogen bridges toward weaker acceptors, such as residues from lysine and serine. Hydrogen peroxide activation occurs in the thermochemical model by side-on binding in orthovanadium peroxoic acid, oxidizing bromide with virtually no activation energy to hydrogen bonded hypobromous acid
-
-
-
additional information
?
-
the disproportionation reaction of hydrogen peroxide is a bromidemediated reaction, i.e. V-BPO does not catalyze the formation of singlet oxygen in the absence of bromide ions
-
-
-
additional information
?
-
vanadium containing bromoperoxidase mimicking (structural and/or functional) activities of vanadium(V) complexes has been reported by several groups in which the active site contains vanadium(V) coordinated to O/N donor ligands. Vanadium(V) complexes catalyze the oxidative bromination of organic substrates into useful halogenated organic compounds in the presence of halide and H2O2 in mild acid medium, just like natural VBrPO enzymes and hence, these are considered as models for VBrPO enzymes. Synthesis, crystal structure, DFT calculations, protein interaction, anticancer potential and bromoperoxidase mimicking activity of oxidoalkoxidovanadium(V) complexes: DFT calculations, protein interaction analysis, circular dichroism study, anticancer activity determination with MCF-7 cells, and determination of mitochondrial membrane potential (MMP) as well as intracellular reactive oxygen species (ROS) production, detailed overview
-
-
-
additional information
?
-
vanadium-dependent bromoperoxidases catalyze reactions involving peroxides and bromide or iodide ions
-
-
-
additional information
?
-
assay method development and evaluation: assay for BrPO (and ClPO) activity, based on the fluorescent probe, [6-(4'-amino)phenoxy-3H-xanthen-3-on-9-yl]benzoic acid [aminophenyl fluorescein (APF)], designed to selectively detect highly reactive oxygen species (hROS), overview. APF-based assays are used in different applications: (i) to demonstrate the generation of highly reactive hypohalite by the partially purified V-BrPO of the red seaweed Corallina officinalis and to establish the temperature response and pH optima for V-BrPO of Corallina officinalis, and (ii) measure BrPO activity in planktonic communities of coastal waters and investigate the size-distribution and temporal change of enzyme rates. In the APF assay, the hypohalite that generates fluorescein will potentially also react with other organic compounds if they are present, including molecules susceptible to electrophilic attack and halogenation. Bromoperoxidase concentration dependence of the dearylation of APF to fluorescein. The APF assay cannot be used to detect iodoperoxidases (IPO) activity. The enzyme from Corallina officinalis is not active with iodide and chloride
-
-
-
additional information
?
-
-
plays an important role in eliminating epiphytic organisms, especially microalgae on the surface. The activity increased during winter and spring and peaked in late spring. Functions to eliminate H2O2 compensating for catalase
-
-
?
additional information
?
-
-
strong brominating aactivity, weak chlorinating and iodating activities, catalyzes both benzylic and aromatic hydroxylations (e.g., of toluene and naphthalene)
-
-
?
additional information
?
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assay method development and evaluation: assay for BrPO (and ClPO) activity, based on the fluorescent probe, [6-(4'-amino)phenoxy-3H-xanthen-3-on-9-yl]benzoic acid [aminophenyl fluorescein (APF)], designed to selectively detect highly reactive oxygen species (hROS), overview. APF-based assays are used in different applications: (i) quantify the BrPO activity in two different species of diatom, Porosira glacialis and Fragilariopsis cylindrus, and (ii) measure BrPO activity in planktonic communities of coastal waters and investigate the size-distribution and temporal change of enzyme rates. In the APF assay, the hypohalite that generates fluorescein will potentially also react with other organic compounds if they are present, including molecules susceptible to electrophilic attack and halogenation. Bromoperoxidase concentration dependence of the dearylation of APF to fluorescein. The APF assay cannot be used to detect iodoperoxidases (IPO) activity
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additional information
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assay method development and evaluation: assay for BrPO (and ClPO) activity, based on the fluorescent probe, [6-(4'-amino)phenoxy-3H-xanthen-3-on-9-yl]benzoic acid [aminophenyl fluorescein (APF)], designed to selectively detect highly reactive oxygen species (hROS), overview. APF-based assays are used in different applications: (i) quantify the BrPO activity in two different species of diatom, Porosira glacialis and Fragilariopsis cylindrus, and (ii) measure BrPO activity in planktonic communities of coastal waters and investigate the size-distribution and temporal change of enzyme rates. In the APF assay, the hypohalite that generates fluorescein will potentially also react with other organic compounds if they are present, including molecules susceptible to electrophilic attack and halogenation. Bromoperoxidase concentration dependence of the dearylation of APF to fluorescein. The APF assay cannot be used to detect iodoperoxidases (IPO) activity
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the alkyl hydroperoxides ethyl hydroperoxide, cuminyl hydroperoxide, and tert-butyl hydroperoxide do not support bromination of dioxygen formation catalyzed by V-BrPO
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no substrate: chloride
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no substrate: chloride
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the natural brominated compound is dibromoacetaldehyde
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the natural brominated compound is dibromoacetaldehyde
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positional specificity of oxidative hydroxybromination for olefins, using rBPO-A1 and PA in the presence of methanol, is higher compared to a non-enzymatic reaction using peracetic acid. The oxidative bromination step, occurring after the enzymatic peroxidation step, is suggested to be pseudoenzymatic. Non-enzymatic oxidative bromination's influence can be disregarded under acidic condition of pH 6.0 or lower because generation of a strongly brominating active species is not the rate-limiting step under acidic conditions
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positional specificity of oxidative hydroxybromination for olefins, using rBPO-A1 and PA in the presence of methanol, is higher compared to a non-enzymatic reaction using peracetic acid. The oxidative bromination step, occurring after the enzymatic peroxidation step, is suggested to be pseudoenzymatic. Non-enzymatic oxidative bromination's influence can be disregarded under acidic condition of pH 6.0 or lower because generation of a strongly brominating active species is not the rate-limiting step under acidic conditions
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additional information
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positional specificity of oxidative hydroxybromination for olefins, using rBPO-A1 and PA in the presence of methanol, is higher compared to a non-enzymatic reaction using peracetic acid. The oxidative bromination step, occurring after the enzymatic peroxidation step, is suggested to be pseudoenzymatic. Non-enzymatic oxidative bromination's influence can be disregarded under acidic condition of pH 6.0 or lower because generation of a strongly brominating active species is not the rate-limiting step under acidic conditions
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production of polyhalogenated carbazoles (PHCs) from halogenation of carbazole in the presence of bromide and/or chloride under the catalysis of chloroperoxidase (CPO) isolated from the marine fungus Caldariomyces fumago, see also EC 1.11.1.10. A total of 25 congeners including mono-to tetra-substituted chlorinated, brominated, and mixed halogenated carbazoles (with substitution patterns of -BrCl, -BrCl2, -BrCl3, -Br2Cl, -Br2Cl2, and -Br3Cl) are produced from the reactions under various conditions. The PHC product profiles are apparently dependent on the halide concentrations. In the CPO-mediated chlorination of carbazole, 3-mono- and 3,6-dichlorocarbazoles predominated in the formation products. In addition to the less abundant mixed halogenated carbazoles (-Br2Cl), 1,3,6-tri- and 1,3,6,8-tetrabromocarbazoles are the dominant products in reactions containing both Br- and Cl-
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CPO is a haeme-thiolate peroxidase requiring the presence of H2O2 to form an activated enzymatic species, responsible for oxidising either halides or organic substrates. CPO catalyses the halogenation of estrogens at comparable rates to other aromatic compounds. See also EC 1.11.1.10
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H2O2 activation of the heme group. LC-MS/MS and gas chromatography-mass spectrometry (GC-MS) are used for product identification, overview. 2,2'-Dihyroxy-3,3',5,5'-tetrabromobiphenyl is also formed in the reactions, but is no substrate itself, no activity with 2,4,6-tribromophenol as a substrate. Evolution of BOC formation from phenol during CPO-mediated oxidation in the presence of bromide overview. Hydroxylated polybrominated diphenyl ethers (diOH-PBDEs) and hydroxylated polybrominated biphenyls (diOH-PBBs) formed by dihydroxyl group substitutions in the ortho-positions relative to the diphenyl ether bond or the single bond in biphenyl, may undergo intramolecular cyclization
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the alkyl hydroperoxides ethyl hydroperoxide, cuminyl hydroperoxide, and tert-butyl hydroperoxide do not support bromination of dioxygen formation catalyzed by V-BrPO
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no activity with Cl-
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no activity with Cl-
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the lowest specific bromoperoxidase activity occurs during the midexponential phase of growth and then increases steeply during the late stationary phase, suggesting that bromoperoxidase production is part of secondary metabolism
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additional information
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assay method development and evaluation: assay for BrPO (and ClPO) activity, based on the fluorescent probe, [6-(4'-amino)phenoxy-3H-xanthen-3-on-9-yl]benzoic acid [aminophenyl fluorescein (APF)], designed to selectively detect highly reactive oxygen species (hROS), overview. APF-based assays are used in different applications: (i) quantify the BrPO activity in two different species of diatom, Porosira glacialis and Fragilariopsis cylindrus, and (ii) measure BrPO activity in planktonic communities of coastal waters and investigate the size-distribution and temporal change of enzyme rates. In the APF assay, the hypohalite that generates fluorescein will potentially also react with other organic compounds if they are present, including molecules susceptible to electrophilic attack and halogenation. Bromoperoxidase concentration dependence of the dearylation of APF to fluorescein. The APF assay cannot be used to detect iodoperoxidases (IPO) activity
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additional information
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assay method development and evaluation: assay for BrPO (and ClPO) activity, based on the fluorescent probe, [6-(4'-amino)phenoxy-3H-xanthen-3-on-9-yl]benzoic acid [aminophenyl fluorescein (APF)], designed to selectively detect highly reactive oxygen species (hROS), overview. APF-based assays are used in different applications: (i) quantify the BrPO activity in two different species of diatom, Porosira glacialis and Fragilariopsis cylindrus, and (ii) measure BrPO activity in planktonic communities of coastal waters and investigate the size-distribution and temporal change of enzyme rates. In the APF assay, the hypohalite that generates fluorescein will potentially also react with other organic compounds if they are present, including molecules susceptible to electrophilic attack and halogenation. Bromoperoxidase concentration dependence of the dearylation of APF to fluorescein. The APF assay cannot be used to detect iodoperoxidases (IPO) activity
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the role of the enzyme is related to its activity as a catalase rather than as a halogenatingt agent
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no substrate: chloride
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no substrate: chloride
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no substrate: chloride
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besides its phytase activity (EC 3.1.3.8) with myo-inositol hexakisphosphate, the enzyme rSt-Phy also shows haloperoxidase activity. Enzyme rSt-Phy brings out a change in color of phenol red from red-orange to blue-violet in the presence of metavanadate ions, H2O2 and KBr in the reaction mixture, which confirms the bromoperoxidation of phenol red. Only histidine acid phosphatases with the active site sequence RHGXRXP can function as haloperoxidase, when vanadate ion is incorporated into the active site. Vanadate is a phosphate analogue, which is generally considered to bind as a transition state analogue to the phosphoryl transfer enzymes and inhibits their activities
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